Queuin

Structural formula
General
Surname	Queuin
other names	Base Q; (1 S , 4 S , 5 R ) -2-Amino-5 - {[(- 4,5-dihydroxy-2-cyclopenten-1-yl) amino] methyl} -1,7-dihydro-4 H -pyrrolo [2,3- d ] pyrimidin-4-one;
Molecular formula	C 12 H 15 N 5 O 3
External identifiers / databases
PubChem	114881
ChemSpider	102837
DrugBank	DB14732
Wikidata	Q424797
properties
Molar mass	277.28 g mol −1
Physical state	firmly
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Queuin is a heterocyclic organic compound . It is a derivative of the nucleobase guanine . The N ⁷ atom of guanine is replaced by a C ⁷ atom and thus forms 7-deazaguanosine , to which a cyclopentene ring has been attached via an aminomethyl group . It occurs as a component of the nucleoside queuosine (Q) in the tRNA .

literature

Walter R. Farkas: Queuine, The Q-Containing tRNAs and the Enzymes Responsible for Their Formation ; Nucleosides, Nucleotides and Nucleic Acids , 1983 , 2 (1), pp. 1-20 ( doi : 10.1080 / 07328318308078845 ).
Hiroshi Akimoto, Eiko Imamiya, Takenori Hitaka, Hiroaki Nomura, Susumu Nishimura: Synthesis of Queuine, the Base of Naturally Occurring Hypermodified Nucleoside (Queuosine), and Its Analogues ; J. Chem. Soc., Perkin Trans. 1 , 1988 , pp. 1637-1644 ( doi : 10.1039 / P19880001637 ).
Charles J. Barnett, Lana M. Grubb: Total Synthesis of Q-Base (Queuine) ; Tetrahedron , 2000 , 56 (47), pp. 9221-9225 ( doi : 10.1016 / S0040-4020 (00) 00895-4 ).
Florian Klepper: Synthesis of the natural tRNA nucleoside modifications queuosine and archaeosine , dissertation, Munich 2007 ( PDF ; 5.1 MB), pp. 25–28.
Allen F. Brooks, George A. Garcia, HD Hollis Showalter: A Short, Concise Synthesis of Queuine ; Tetrahedron Letters , 2010 , 51 (32), pp. 4163-4165 ( doi : 10.1016 / j.tetlet.2010.06.008 ; PDF ).

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

Entry for Queuine in the Human Metabolome Database (HMDB) , accessed June 12, 2019.